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Volumn 14, Issue 22, 2008, Pages 6704-6712

Fragmentation of carbohydrate anomeric alkoxyl radicals: New synthesis of chiral 1-fluoro-1-halo-1-iodoalditols

Author keywords

Alditols; Asymmetric synthesis; Carbohydrates; Halogens; Radical reactions

Indexed keywords

CARBOHYDRATES; CHEMICAL REACTIONS; FLUORINE; IODINE; ORGANIC COMPOUNDS;

EID: 53849109914     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800734     Document Type: Article
Times cited : (26)

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    • Throughout this section, the numbering of the trihaloalditols has always begun at the carbon atom bearing the halogens, although the correct IUPAC systematic nomenclature has been used in the Experimental Section and Supporting Information
    • Throughout this section, the numbering of the trihaloalditols has always begun at the carbon atom bearing the halogens, although the correct IUPAC systematic nomenclature has been used in the Experimental Section and Supporting Information.
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    • CCDC-679904, S)-54) and 219090, S)-55 contain the supplementary crystallographic data (excluding structure factors) for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_ request/cif. Crystal data and structure refinements Compound (S)-54: C16H15ClFIN2O10; M T, 576.65; monoclinic: space group, C2; a, 29.7995(13, b, 6.5809(3, c, 10.4310(3) Å; β, 96.422(2)°; V=2032.76(15) Å3; Z, 4; pcalcd= 1.884 mg cm-3; μ(Mokα, 0.71073 Å; F(000, 1136; T= 123(2) K; colourless crystal, 0.18 × 0.18 × 0.07 mm, collected reflections 21338. The structure was solved by direct methods, all hydrogen atoms were refined anisolropically by using full-matrix least-squa
    • o|)) and 284 parameters. Selected structural data: O-C2-C1-I = -66.6, O-C2-C1-Br = 56.8, O-C2-C1-F = 171.8°.
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